This research study focuses on retention of First-Year students with a qualitative approach to collecting data. The purpose of this study was to explore lived experiences of sophomore students who were retained between their first and second year at their university. The four sophomore participants reflect on their first-year student experiences to provide a deeper understanding of retention from the student prospective. This research will explore the ways in which the sophomore participants make sense of their college transition and how they responded to surprises during their first-year experience as a student on their campus using the organizational theory Sensemaking and Surprise by Louis (1980). The four sophomore participants contributed to the findings through their reflections of the first-year student experiences on their individual college campuses. Each student provided data through two interview meetings and email. The following document shares their stories using Narrative Inquiry as the research methodology. Their unique experiences provide insight on shared transition challenges they faced on their campuses. The conclusions and implications shared from this data can assist those who are interested in the transition and retention of first-year college students.